Methanol → HCID 19937767, compound

HRID 36763

Reaction equation

HRID 36763 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:20])[CH2:15][S:16][C:17](=O)[CH3:18])([CH3:3])[CH3:2].CO.[OH-].[Na+].BrCC[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:40][CH2:39]1>C(OCC)(=O)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:20])[CH2:15][S:16][CH2:17][CH2:18][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:41]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:40][CH2:39]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 15289526HCID 15289526, compoundHCID 199377541-Bromo-12-(4-phenylpiperazinyl)dodecane

Product 1

HCID 19937767HCID 19937767, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1.47 g of N-(2,6-diisopropylphenyl)-2-(acetylthio)acetamide and 12 ml of methanol was added dropwise 1.7 ml of a 30% aqueous sodium hydroxide solution at 0° C. in an argon atmosphere. After stirring for 30 minutes, a mixture of 2.05 g of 1-bromo-12-(4-phenylpiperazinyl)dodecane synthesized in (1) above and 14 ml of methanol was added thereto, followed by stirring at 60° C. for 1 hour and then at room temperature for 16 hours. To the reaction mixture was added 100 ml of ethyl acetate, and the mixture was washed successively with water and a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography using a 1:2 mixture of ethyl acetate and hexane as a developing solvent. The resulting crystals were recrystallized from isopropyl alcohol-water to yield 1.66 g of the title compound as white powder (m.p.=76.5° -77.5° C.).

Workup

  1. stirringby stirring at 60° C. for 1 hour
  2. waitat room temperature for 16 hours
  3. washthe mixture was washed successively with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additiona 1:2 mixture of ethyl acetate and hexane as a developing solvent
  7. customThe resulting crystals were recrystallized from isopropyl alcohol-water

Sources & evidence

ORD record
ord-84b459ec96ee44ad9b0841d016b96fa3
Source dataset
uspto-grants-1995_05
Patent number
US05416212

Linked notes

Loading…